p-Toluenesulfonyl isocyanate → HCID 13423329, compound

HRID 1284472Notes

Reaction equation

HRID 1284472 reaction equation
[C:1]1(/[C:7](/[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]1([CH3:33])[CH:26]=[CH:25][C:24]([S:27]([N:30]=[C:31]=[O:32])(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[C:21]1([CH3:33])[CH:22]=[CH:23][C:24]([S:27]([NH:30][C:31]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]/[CH:8]=[C:7](\[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)/[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:32])(=[O:28])=[O:29])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 13417327HCID 13417327, compound

Product 1

HCID 13423329HCID 13423329, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-7-Phenyl-7-(3-pyridyl)-6-hepten-1-ol (2.0 g, 7.4 mmoles) was dissolved in methylene chloride (20 ml), and p-toluenesulfonyl isocyanate (1.5 g, 7.6 mmoles) was added to the solution. The mixture was stirred at room temperature for an hour and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography using isopropyl ether-ethyl acetate (1:1) as the developing solvent. Recrystallization of the product from ethyl acetate gave 1-(p-toluenesulfonyl)aminocarbonyloxy-(E)-7-phenyl-7-(3-pyridyl)-6-heptene (2.1 g, 60%) (Compound Id-29).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customRecrystallization of the product from ethyl acetate

Sources & evidence

ORD record
ord-b51538c01ea54ec1a2c5c16b56fcf46d
Source dataset
uspto-grants-1986_01
Patent number
US04563446

Reaction notes

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